Trifluoroacetic acid → 6-Aminoquinoline

HRID 1520162Notes

Reaction equation

HRID 1520162 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11]C(=O)OC(C)(C)C)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22318072HCID 22318072, compound

Product 1

HCID 113736-AminoquinolineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-(quinolin-6-yl)carbamate (1.3 g, 5.32 mmol) in DCM (40 ml) was added TFA (10 ml) with stirring overnight at room temperature. The resulting mixture was concentrated under vacuum, diluted with water (30 ml), adjusted pH to 8 with NaHCO3 solution, extracted with dichloromethane (2×20 ml), dried over magnesium sulfate and concentrated in vacuo to give quinolin-6-amine as a yellow solid (666 mg, 87%).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additiondiluted with water (30 ml)
  3. extractionextracted with dichloromethane (2×20 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b13405da997a4a28927abc66e142318a
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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